飽和脂肪酸のオゾン酸化
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概要
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Lauric, myristic, palmitic, and stearic acids were oxidized with an ozone-oxygen mixture (fatty acid : ozone, 1 : 3 mol) at 90°C in acetic acid-water (9 : 1 vol/vol). Fatty acid conversion ranged from 80 to 95%, increasing in the order of stearic, palmitic, myristic and lauric acid.<BR>Most of the products consisted of dicarboxylic acid, as a major product but mono- and oxocarboxylic acids were also formed. Dicarboxylic acid (C<SUB><I>n</I></SUB>H<SUB>2<I>n</I>-2</SUB>O<SUB>4</SUB>) produced from lauric acid was <I>n</I>=310 and from myristic, palmitic, and stearic acid, <I>n</I>=312. The mono- and dicarboxylic acids formed in large amounts were mainly those having the half numbers of carbon atoms of starting fatty acids. In the reactions, oxocarboxylic acid was initially formed in large quantities but decreased with time, while the amount of dicarboxylic acid increased.<BR>The following processes were noted to occur during the course of the reactions : <BR>1) Oxidation of a carbon atom located about center of hydrocarbon chain of the fatty acid to form oxocarboxylic acid.<BR>2) The oxidative cleavage of this acid to form mono- and dicaboxylic acid.
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